US3096142A - Process for dye levelling with lactams - Google Patents

Process for dye levelling with lactams Download PDF

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Publication number
US3096142A
US3096142A US747351A US74735158A US3096142A US 3096142 A US3096142 A US 3096142A US 747351 A US747351 A US 747351A US 74735158 A US74735158 A US 74735158A US 3096142 A US3096142 A US 3096142A
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United States
Prior art keywords
dyeing
parts
lactam
levelling
radicals
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Expired - Lifetime
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US747351A
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English (en)
Inventor
Hartmark Bjarne
Schuster Curt
Herrle Karl
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the object of the invention is to provide dyeing axuiliaries which above all are especially active and productive as levelling agents.
  • a further object of the invention is to carry out levelling with dyeing auxiliaries which do not disturb the dyeing process.
  • a further object of the invention is the use of the dyeing auxiliaries for subsequent levelling (levelling out) dyeings which are not level.
  • the objects of the invention are achieved by compounds which contain in the molecule at least two lactam radicals which are connected through their nitrogen atoms by a carbon chain interrupted by at least one hetero atom, the number of carbon atoms between a lactarn nitrogen atom and the hetero atom being 2 to 6.
  • the said lactarn radicals may contain 5, 6 or 7 ring members, i.e. they may be the radicals of butyrolactam, valerolactam or caprolactam.
  • the lactam radicals may also hear substituents on the carbon atoms, as, for example, alkyl radicals.
  • Alkyl radicals with only a few carbon atoms, as for example the methyl, ethyl or propyl radicals, may be the substituents.
  • the lactam radicals in the dyeing auxiliaries may be identical or different.
  • the hetero atoms by which the carbon chains between the lactam radicals are interrupted are nitrogen, oxygen or sulfur atoms.
  • the third linkage of the nitrogen atom my be combined with a hydrogen atom or with an aliphatic or cycloaliphatic radical.
  • the length of this aliphatic radical may amount to 1 to 5, preferably 1 to 4, carbon atoms.
  • the aliphatic radical may also bear further radicals, for example a hydroxyl group which may also be etherified, a nitrilc group, an amino group or a lactam radical.
  • the number of hetero atoms, i.e. of nitrogen, oxygen or sulfur atoms, in the carbon chain between the lactam radicals may be for example 1, 2, 3, 4, 5, 10 or 20, or even more.
  • the hetero atoms may be identical or different.
  • L represents identical or different lactam radicals derived from butyrolactam (pyrrolidone) valerolactam or caprolactam
  • R represents a chain of from 2 to 6 carbon atoms in length
  • R represents a chain of from 1 to 6 carbon atoms in length
  • n 0, 1, 2, 3, 4, 5, or any further integer up to 10, 20 or more
  • X represents 1, 2, 3, or all of the groups --N, N, 0- or S R being an aliphatic radical of l to 5, preferably 1 to 4, carbon atoms in length, which radical may bear other substituents or a cycloaliphatic radical, for example cyclopentyl.
  • R is: methyl, ethyl, propyl,
  • n being any number from 2 to 6, identical or difierent n' may also be 1.
  • Lactam compounds of the said kind are obtained, for example, by reaction of symmetrical dichlordiethyl ether or symmetrical dichlordiethylthioether with a lactam, for example with pyrrolidone or caprolactam, or by reaction of tri-(chlorethyU-amine with the said lactams or by reaction of polyalkylene polyamines, as for example diethylene triamine, N-rnethyl-diethylene triamine, triethylene tetramine or the corresponding propylene derivatives, with lactones, such as butyrolactone or valerolactone.
  • lactones such as butyrolactone or valerolactone.
  • lactones such as butyrolactone or valerolactone.
  • lactones such as butyrolactone or valerolactone.
  • lactones such as butyrolactone or valerolactone.
  • lactones such as butyrolactone or valerolactone.
  • the dyeing auxiliaries used according to this invention contain in the molecule at least two lactam radicals, that, moreover, outside the lactam radical there is in each molecule at least one hetero atom and each lactam radical has at least two additional carbon atoms in the connecting chain. There may also be present in the connecting chain more additional carbon atoms or two or more additional hetero atoms per lactam radical may be present in the connecting chain. Besides the lactam compounds described in detail above, there may also often be used with special advantage the products further modified by adding low molecular weight organic radicals.
  • the lactam compounds containing nitrogen as the hetero atom in the connecting chain there can be obtained products with changed retardation action and those with specially favorable levelling properties.
  • the alkylation may be with aliphatic radicals which contain not more than 5 carbon atoms.
  • halogen-paraffins such as methyl, ethyl or propyl chloride
  • alkylene oxides especially ethylene and propylene oxide, or acrylonitrile. If the nitrile groups contained on the nitrogen atom in such lactam compounds are hydrogenated to the corresponding gamma-amino compounds, highly active products are also obtained.
  • lactam compounds which contain in the connecting chain with dihalogen parafiins, as for example ethylene chloride, dichlordimethyl or dichlordiethyl ether. In this way there are obtained lactam compounds which contain at least four lactam radicals in the molecule.
  • dihalogen parafiins as for example ethylene chloride, dichlordimethyl or dichlordiethyl ether.
  • cyanoethyl groups ethyl-nitrile groups
  • hydrogen atoms attached to the nitrogen atoms.
  • the resultant nitrile derivatives are catalytically hydrogenated under known conditions to form the corresponding polyamines which are then reacted with lactones.
  • radicals L represent identical or different of the said lactam radicals.
  • the dyeing auxiliaries according to this invention have an excellent levelling action in dyeing and on dyeings, for example with vat dyestuffs and sulfur dyestuffs.
  • the agents have no pronounced surfaceactive properties; they do not froth and wet in the concentrations necessary for levelling. They have a basic reaction when they contain nitrogen atoms in the connecting chain. It is possible to dye in the presence of the said dyeing auxiliaries, but they may also be used for a levelling aftertreatrnent of unequal dyeings.
  • the auxiliaries may be used in amounts of 0.1 to 20 grams per litre, preferably 0.25 to 1 gram per litre.
  • the subject dyeing auxiliaries are preferably added after the vatting of the dyestuff.
  • the auxiliary is added to the development bath.
  • the new dyeing auxiliaries are suitable for all hitherto known dyeing methods in which vat and sulfur dyestuffs are used for dyeing.
  • the cause of this is that the agent in bath (b) strips the dyestuff from the dyed cotton but does not allow it to be absorbed, or absorbed to the same extent, by the initially undyed cotton.
  • the dye equalizing action of the agent used in bath (b) is thus small (small leveling action) and, moreover, this agent also retains the dyestuff in the bath (strong retarding action).
  • the catalyst is filtered off, the solvent evaporated in vacuo and the residue (460 parts), which is penta-aminopropyl-dipropylene triamine, is reacted under the conditions described under V(a) with 475 parts of butyrolactonc (5.5 mols).
  • a dark tough resin is obtained which is readily and clearly water-soluble.
  • Example 1 Mereerized cotton yarn which has previously been dyed with 2 percent of the dyestufi of the constitution:
  • Example 2 The superior action of the agents used according to this invention may be seen from the following comparative tests.
  • a blank vat is prepared which contains in each liter 5 grams of sodium dithionite and 12 cc. of caustic soda of 38 Baum strength. Into this vat:
  • Example 3 Staple fiber yarn is dyed on a mechanical yarn dyeing machine (according to Gerber) according to the IN method in a goods to liquor ratio of 1:30 with 2 percent of Indanthren Brilliant Green B (powder, fine, highly concentrated, for dyeing) (C.I. 59825/1956), the dyebath receiving an addition of 1 gram per liter of the product obtainable according to IV from 2 moles of gammaethyl-butyrolactone and l rnol of triethylene tetramine.
  • the dyestutf goes on to the fiber slowly and uniformly.
  • the dyestulf is free from froth and the yarn does not float.
  • the final liquor contains relatively little dyestuff.
  • the yarns are dyed in a level manner and well through.
  • the dyestutf goes on so quickly that the dyeing is not level.
  • a surface-active leveling agent of the type of a hydroxyethylated fatty alcohol or fatty amine or quaternary surface-active ammonium compounds are used it is true that level dyeings are also obtained but too much dyestuff remains in the residual liquor and the dyebath foams, so that the yarns begin to float on the bath. The mechanical manipulation is thereby hindered and the dyeing made impossible.
  • dior tripyrrolidone compounds obtainable according to V(a) and (b) which have oxygen atoms as hetero atoms between the lactam rings. They differ from the first-mentioned agents in that their retarding action is even less.
  • Example 4 Cheeses spools or warp beams of cotton are dyed in a closed dyeing apparatus (according to Obermeier) according to the IN method in the goods to liquor ratio of 1:10 with 1 percent of Indanthren Blue BC Powder, fine ,for dyeing (Cl. 69825/1956). With an otherwise identical method of operation, 1.5 grams per liter of the product prepared according to II(a) are added to the dyebath as the sole leveling agent. After finishing off as usual, the dyed wound bodies are dyed through with good equality, clear shade and unobjectionable uniformity. Only a little dyestulr' remains in the dyebath.
  • Example 5 Cotton waterproof popline is dyed on the automatic jigger, and indeed the fabric previously padded on the foulard with 1 percent of Indanthren Olive T (powder, fine, for dyeing) (C.I. 69525/1956) is developed in the goods to liquor ratio 1:5 on the jigger by the IN method.
  • the development bath apart from the usual additions of hydrosulfite, caustic soda solution and padding liquor, receives no addition of auxiliaries other than 2 grams per liter of the product prepared according to I (a). With a slight retardation action there is obtained a level, well through-dyed and remarkably solid toning.
  • Example 6 A cotton yarn dyed with 2 percent of Indanthren Blue- Green FFB (powder, fine, for dyeing) (Cl. 70305/ 1956) is treated together with the same amount of undyed yarn of the same kind in a blank dyebath according to the IN method in the goods to liquor ratio 1:30 for hour.
  • the object is that after treatment the two yarns should have the same shade of color and the same depth of color (equalization).
  • Example 7 5 to grams per liter of the reaction product of symmetrical dichlordiethyl thioether with pyrrolidone, which is also obtainable in the manner described in VI, are added in the continuous dyeing of cotton piece goods with vat dyestuffs by the pad-steam method. A considerably more level and better dyed-through goods are obtained with a high dyestufi yield, than without the said addition.
  • Example 8 Staple fiber yarn is dyed in the vat with percent Immedial Indoviolet B extra (CI. 53440) in a goods to liquor ratio of 1:30 at 95 C. with 8 percent of soda, 60 percent of sodium sulfide, 50 percent of Glaubers salt for 1 /2 hours.
  • the dyeing tends to bronze, is not fast to rubbing and is unequal.
  • a dyeing free from objection is achieved by the addition of 0.5 to 1 gram per liter of the product prepared according to 1(a).
  • Example 9 Cotton tricot is dyed on the reel vat with 0.22 percent of lndanthren Blue 3 GN powder ((3.1. 69840/ 1956) by the normal dyeing method.
  • the dyeing is unequal. If, however, 0.5 gram per liter of the piperidone compound from 2 mols of valerolactone and 1 mol of diethylene triamine according to IV or a pyrrolidone compound substituted at the hetero atom by an alkyl group according to II(b) be added to the dyebath, the dyeing is considerably more solid and is unobjectionably level by an otherwise identical manner of operation.
  • levelling agent has the formula IIgC-CO COCII2 /NC HrCHr-NII-C HrOIIrNH- OHn-C Hr-N HaC-Clh CH -OH:
  • levelling agent has the formula HnC-CO CO-CH! N-CHz-CIIz-N-CHrCHrNCHrCHr-N H: CH: H: Ha IEC- H H1 H 5N N 6.
  • levelling agent has the formula 7.
  • the levelling agent has the formula 8.
  • the levelling agent has the formula 9.
  • the levelling agent has the formula 10.
  • the step which comprises levelling the dyeings in an alkaline bath with a compound which contains at least two lactam groups with from 5 to 7 ring members in the molecule, the said compound containing between any two lactam groups a connecting chain which has either end linked to the nitrogen atom of the lactam groups, which connecting chain includes at least one heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, the said lactam groups and the said heteroatoms being connected by a. carbon chain containing from 2 to 6 carbon atoms, and the said heteroatoms being connected to each other by carbon chains containing from 1 to 6 carbon atoms.
  • levelling process according to claim 10 wherein the levelling agent has from 3 to 5 lactam groups.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US747351A 1957-07-10 1958-07-09 Process for dye levelling with lactams Expired - Lifetime US3096142A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB45256A DE1133695B (de) 1957-07-10 1957-07-10 Egalisiermittel in der Textilfaerberei

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US3096142A true US3096142A (en) 1963-07-02

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US (1) US3096142A (enrdf_load_stackoverflow)
CH (1) CH355434A (enrdf_load_stackoverflow)
DE (1) DE1133695B (enrdf_load_stackoverflow)
GB (1) GB834393A (enrdf_load_stackoverflow)
NL (2) NL229439A (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3312691A (en) * 1963-08-23 1967-04-04 Ciba Geigy Corp 2, 3, 4, 5-tetrahydro-1-benzazepin-2-ones
US3753647A (en) * 1970-03-05 1973-08-21 North American Rockwell Liquid oxygen compatible dye penetrant method for metal defect inspection
US4083689A (en) * 1974-09-26 1978-04-11 Bayer Aktiengesellschaft Solid ε-caprolactam dyestuff preparations
US4120648A (en) * 1975-12-23 1978-10-17 Ciba-Geigy Corporation Dye preparation
US4311481A (en) * 1981-01-23 1982-01-19 Nelson Research & Development Company Method for improved dyeing
US4450102A (en) * 1982-11-02 1984-05-22 Phillips Petroleum Company Sulfur based metal cleaners and corrosion inhibitors

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3369855A (en) * 1960-10-29 1968-02-20 Basf Ag Levelling sulfur and vat dyes with low molecular weight polyamides
CH380078A (de) * 1961-06-12 1962-12-29 Ciba Geigy Verwendung von Polyamiden als Egalisiermittel für Küpenfärbungen
US3326628A (en) * 1963-06-21 1967-06-20 Ciba Ltd Vat dyeing with ethylene urea-formaldehyde type resin treatment

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE524317A (enrdf_load_stackoverflow) * 1953-01-26
US2225604A (en) * 1939-06-13 1940-12-17 Du Pont Coloring composition
US2282724A (en) * 1936-11-03 1942-05-12 Gen Aniline & Film Corp Process of dyeing with substantive colors
US2555354A (en) * 1949-01-14 1951-06-05 Sterling Drug Inc 1-aliphatic-3, 3-diphenyl-2-pyrrolidones and process for preparing same and related products
US2775599A (en) * 1952-04-10 1956-12-25 Schenley Ind Inc Process for the production of n-vinylpyrrolidone-2
US2955008A (en) * 1953-07-27 1960-10-04 Gen Aniline & Film Corp Dyeing of polyacrylonitrile fibrous material

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE871154C (de) * 1942-08-26 1953-03-19 Basf Ag Verfahren zur Herstellung oberflaechenwirksamer Verbindungen
DE818042C (de) * 1949-04-22 1951-10-22 Basf Ag Textil- und Faerbereihilfsmittel
GB735396A (en) * 1952-06-21 1955-08-17 Celanese Corp Vat dyeing
DE955409C (de) * 1952-09-22 1957-01-03 British Celanese Verfahren zum voruebergehenden Faerben von Textilmaterialien und Farbstoffpraeparat hierfuer

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2282724A (en) * 1936-11-03 1942-05-12 Gen Aniline & Film Corp Process of dyeing with substantive colors
US2225604A (en) * 1939-06-13 1940-12-17 Du Pont Coloring composition
US2555354A (en) * 1949-01-14 1951-06-05 Sterling Drug Inc 1-aliphatic-3, 3-diphenyl-2-pyrrolidones and process for preparing same and related products
US2775599A (en) * 1952-04-10 1956-12-25 Schenley Ind Inc Process for the production of n-vinylpyrrolidone-2
BE524317A (enrdf_load_stackoverflow) * 1953-01-26
US2955008A (en) * 1953-07-27 1960-10-04 Gen Aniline & Film Corp Dyeing of polyacrylonitrile fibrous material

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3312691A (en) * 1963-08-23 1967-04-04 Ciba Geigy Corp 2, 3, 4, 5-tetrahydro-1-benzazepin-2-ones
US3753647A (en) * 1970-03-05 1973-08-21 North American Rockwell Liquid oxygen compatible dye penetrant method for metal defect inspection
US4083689A (en) * 1974-09-26 1978-04-11 Bayer Aktiengesellschaft Solid ε-caprolactam dyestuff preparations
US4120648A (en) * 1975-12-23 1978-10-17 Ciba-Geigy Corporation Dye preparation
US4311481A (en) * 1981-01-23 1982-01-19 Nelson Research & Development Company Method for improved dyeing
US4450102A (en) * 1982-11-02 1984-05-22 Phillips Petroleum Company Sulfur based metal cleaners and corrosion inhibitors

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Publication number Publication date
GB834393A (en) 1960-05-04
DE1133695B (de) 1962-07-26
CH355434A (de) 1961-07-15
NL229439A (enrdf_load_stackoverflow)
NL100272C (enrdf_load_stackoverflow)

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